The pleated waist and side pockets add a feminine touch to a masculine-inspired pant. Just picture them paired with a pair of wedged ankle boots! ($51, mikkatmarket.com)

Reveal your playful side with this adorable pleated mini, perfect for winter layering. ($40, zara.com)

When the Fall ’09 collections debuted, I drooled over the rich satin folds at Balenciaga, especially an indigo and black skirt–traditionally a tricky shade combo. These pleated satin flats from Urban Outfitters ($32, visit urbanoutfitters.com) are an effortless way to try out the combination and add sheen to basic holiday black. They also come in [...]